EP1076053A1 - Derives du 3-arylphenyl-sulfure, insecticides et acaricides - Google Patents

Derives du 3-arylphenyl-sulfure, insecticides et acaricides Download PDF

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Publication number
EP1076053A1
EP1076053A1 EP99917160A EP99917160A EP1076053A1 EP 1076053 A1 EP1076053 A1 EP 1076053A1 EP 99917160 A EP99917160 A EP 99917160A EP 99917160 A EP99917160 A EP 99917160A EP 1076053 A1 EP1076053 A1 EP 1076053A1
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poly
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EP99917160A
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German (de)
English (en)
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EP1076053A4 (fr
EP1076053B1 (fr
Inventor
Keiji K&bull I Chem. Rch. Inst. CO. Ltd TORIYABE
Nobuo K&bull I Chem. Rch. Inst. Co. Ltd TAKEFUJI
Minoru K&bull I Chem. Rch. Inst. Co. Ltd. ITOU
Tetsuya K&bull I Chem. Rch. Inst. Co. Ltd HIRADE
K&bull I Chem Rch Inst Co Ltd NISHIYAMA Kiyotoshi
Mitsuharu K&bull I Chem Rch Inst Co. Ltd ASAHIDA
Yasunobu K&bull I Chem. Rch. Inst. Co. Ltd MAEDA
Nobuhide K&bull I Chem. Rch. Inst. Co. Ltd. WADA
Toyokazu Fujisawa
Hiroyuki Yano
Masaaki Komatsu
Osamu Tada
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Ihara Chemical Industry Co Ltd
Kumiai Chemical Industry Co Ltd
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Ihara Chemical Industry Co Ltd
Kumiai Chemical Industry Co Ltd
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Publication of EP1076053A1 publication Critical patent/EP1076053A1/fr
Publication of EP1076053A4 publication Critical patent/EP1076053A4/fr
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Publication of EP1076053B1 publication Critical patent/EP1076053B1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/08—Preparation by ring-closure
    • C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
    • C07D213/12—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from unsaturated compounds
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    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
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    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/48—Aldehydo radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • L 3 is a halogen atom
  • Ar is a group represented by general formula (Ar-1) or general formula (Ar-3)
  • B 0 to B 3 , R and n are the same as defined above.
  • a compound represented by general formula (XIII) yields a 3-arylphenyl sulfide derivative represented by general formula (I-2) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (XIV) in from 0.5 to 10l of a solvent in the presence of from 1 to 5 moles of a base (the same as defined for Process 1), in relation to 1 mole of the compound represented by general formula (XIII).
  • Each reaction is carried out at an arbitrary temperature within the range of from -70°C to the reflux temperature of the reaction system, preferably from -20°C to 100°C, and completed in from 10 minutes to 20 hours, depending on the compound.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
EP99917160A 1998-04-27 1999-04-26 Derives du 3-arylphenyl-sulfure, insecticides et acaricides Expired - Lifetime EP1076053B1 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
JP13276898 1998-04-27
JP13276898 1998-04-27
JP28353998 1998-09-18
JP28353998 1998-09-18
JP30958098 1998-10-30
JP30958098 1998-10-30
PCT/JP1999/002212 WO1999055668A1 (fr) 1998-04-27 1999-04-26 Derives du 3-arylphenyl-sulfure, insecticides et acaricides

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EP1076053A1 true EP1076053A1 (fr) 2001-02-14
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EP (1) EP1076053B1 (fr)
AU (1) AU3536699A (fr)
DE (1) DE69934224T2 (fr)
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EP1803712A1 (fr) * 2004-10-20 2007-07-04 Kumiai Chemical Industry Co., Ltd. Dérivé de 3-triazolylphénylsulfide et insecticide/acaricide/nématicide incluant ledit dérivé au titre de principe actif
EP1803712A4 (fr) * 2004-10-20 2009-08-26 Kumiai Chemical Industry Co Dérivé de 3-triazolylphénylsulfide et insecticide/acaricide/nématicide incluant ledit dérivé au titre de principe actif
KR101310073B1 (ko) * 2004-10-20 2013-09-24 이하라케미칼 고교가부시키가이샤 3-트리아졸릴페닐설파이드 유도체 및 그것을유효성분으로서 함유하는 살충·살진드기·살선충제
US7872036B2 (en) 2004-10-20 2011-01-18 Kumiai Chemical Industry Co., Ltd. 3-triazolylphenyl sulfide derivative and insecticide, miticide and nematicide containing it as an active ingredient
TWI382020B (zh) * 2004-10-20 2013-01-11 Kumiai Chemical Industry Co ３-三唑基苯基硫醚衍生物及以其為有效成份之殺蟲、殺蟎、殺線蟲劑
AU2005296529B2 (en) * 2004-10-20 2011-03-24 Ihara Chemical Industry Co., Ltd. 3-triazolylphenyl sulfide derivative and insecticide/acaricide/nematicide containing the same as active ingredient
GB2423518A (en) * 2005-02-28 2006-08-30 Takasago Perfumery Co Ltd Platinum complex and light-emitting device
WO2010100189A1 (fr) * 2009-03-04 2010-09-10 Basf Se Composés de 3-arylquinazolin-4-one pour lutter contre les organismes nuisibles invertébrés
CN102341376A (zh) * 2009-03-04 2012-02-01 巴斯夫欧洲公司 用于防治无脊椎动物害虫的3-芳基喹唑啉-4-酮化合物
US8765774B2 (en) 2009-03-04 2014-07-01 Basf Se 3-arylquinazolin-4-one compounds for combating invertebrate pests
CN102471290A (zh) * 2009-07-16 2012-05-23 拜尔农作物科学股份公司 手性3-三唑基亚砜衍生物的制备方法
AU2010272874B2 (en) * 2009-07-16 2015-01-15 Bayer Intellectual Property Gmbh Use of phenyl triazoles for controlling insects and spider mites by splashing, misting or immersion or by treatment of seeds
WO2011006605A1 (fr) * 2009-07-16 2011-01-20 Bayer Cropscience Aktiengesellschaft Utilisation de phényltriazoles pour lutter contre les insectes et les tétranyques par arrosage, application au goutte-à-goutte ou immersion, ou encore par traitement des semences
TWI471314B (zh) * 2009-07-16 2015-02-01 Bayer Cropscience Ag 製備對掌性３－三唑基亞碸衍生物之方法
WO2011006646A1 (fr) * 2009-07-16 2011-01-20 Bayer Cropscience Ag Procédé de préparation de dérivés 3-triazolyl-sulfoxyde chiraux
CN102471290B (zh) * 2009-07-16 2016-02-03 拜耳知识产权有限责任公司 手性3-三唑基亚砜衍生物的制备方法
CN102469787A (zh) * 2009-07-16 2012-05-23 拜尔农作物科学股份公司 苯基三唑通过浇水、弥雾或浸渍或者通过处理种子而用于防治昆虫和叶螨的用途
US8765970B2 (en) 2009-07-16 2014-07-01 Bayer Cropscience Ag Process for preparing chiral 3-triazolyl sulphoxide derivatives
US8314133B2 (en) 2009-07-16 2012-11-20 Bayer Cropscience Ag Process for preparing chiral 3-triazolyl sulphoxide derivatives
JP2012532906A (ja) * 2009-07-16 2012-12-20 バイエル・クロップサイエンス・アーゲー キラル３−トリアゾリルスルホキシド誘導体を調製する方法
EP2274982A1 (fr) * 2009-07-16 2011-01-19 Bayer CropScience AG Utilisation de phényltriazole pour combattre les insectes et les tétranyques par arrosage, application au goutte-à-goutte ou par immersion ou par le traitement de semences
WO2011020579A1 (fr) * 2009-08-20 2011-02-24 Bayer Cropscience Ag Procédé de préparation de 1-phényl-1,2,4-triazoles
US20110046194A1 (en) * 2009-08-20 2011-02-24 Bayer Cropscience Ag 3-Triazolylphenyl-substituted sulphide derivatives as acaricides and insecticides
WO2011020567A1 (fr) * 2009-08-20 2011-02-24 Bayer Cropscience Ag Dérivés de sulfure à substitution 3-triazolylphényle comme acaricides et insecticides
CN102573479B (zh) * 2009-08-20 2015-04-22 拜尔农作物科学股份公司 用作杀螨剂和杀昆虫剂的3-[1-(3-卤代烷基)三唑基]苯基硫化物衍生物
US8722717B2 (en) 2009-08-20 2014-05-13 Bayer Cropscience Ag 3-triazolylphenyl-substituted sulphide derivatives as acaricides and insecticides
CN102573479A (zh) * 2009-08-20 2012-07-11 拜尔农作物科学股份公司 用作杀螨剂和杀昆虫剂的3-[1-(3-卤代烷基)三唑基]苯基硫化物衍生物
CN102471291A (zh) * 2009-08-20 2012-05-23 拜尔农作物科学股份公司 用作杀螨剂和杀昆虫剂的3-三唑基苯基取代的硫化物衍生物
CN102471291B (zh) * 2009-08-20 2015-04-22 拜尔农作物科学股份公司 用作杀螨剂和杀昆虫剂的3-三唑基苯基取代的硫化物衍生物
WO2011029506A1 (fr) * 2009-08-20 2011-03-17 Bayer Cropscience Ag Dérivés de sulfure de 3-[1-(3-haloalkyl) triazolyl]-phényle comme acaricides et insecticides
WO2012176856A3 (fr) * 2011-06-24 2013-06-13 Ishihara Sangyo Kaisha, Ltd. Pesticide
WO2013030319A2 (fr) 2011-09-02 2013-03-07 Basf Se Utilisation de dérivés pesticides actifs de 3-arylquinazoline-4-one dans des méthodes d'application au sol
WO2013030338A2 (fr) 2011-09-02 2013-03-07 Basf Se Mélanges agricoles comprenant des composés d'arylquinazolinone
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CN105431434A (zh) * 2013-06-04 2016-03-23 拜耳作物科学股份公司 作为害虫防治剂的二环芳基硫化物和芳基亚砜衍生物
WO2014202510A1 (fr) * 2013-06-20 2014-12-24 Bayer Cropscience Ag Dérivés d'arylsulfure et d'arylsulfoxyde utilisés comme acaricides et insecticides
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US9981940B2 (en) 2013-06-20 2018-05-29 Bayer Cropscience Aktiengesellschaft Aryl sulfide derivatives and aryl sulfoxide derivatives as acaricides and insecticides
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US6858639B2 (en) 2005-02-22
DE69934224T2 (de) 2007-10-04
US20050171097A1 (en) 2005-08-04
US6509354B1 (en) 2003-01-21
AU3536699A (en) 1999-11-16
US20090170883A1 (en) 2009-07-02
US7767626B2 (en) 2010-08-03
EP1076053A4 (fr) 2004-11-10
US7037930B2 (en) 2006-05-02
US20030069242A1 (en) 2003-04-10
WO1999055668A1 (fr) 1999-11-04
US7612105B2 (en) 2009-11-03
EP1076053B1 (fr) 2006-11-29
US20050107383A1 (en) 2005-05-19

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